


Home Again

by JanaNa



Category: Supernatural
Genre: AU, Alternate Universe - Criminals, Angst, F/M, M/M, Unresolved Sexual Tension, Violence
Language: English
Status: In-Progress
Published: 2013-11-15
Updated: 2014-01-16
Packaged: 2018-01-01 15:01:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence
Chapters: 5
Words: 11,909
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1045292
Author URL: https://archiveofourown.org/users/JanaNa/pseuds/JanaNa
Summary: <blockquote class="userstuff">
              <p>The Dean sitting in the smoky, dark bar in ripped jeans and faded black T-shirt was very different from the Dean sitting in his twenty-second-floor office in a flattering gray suit and black tie. It was much like the difference between the Dean that conferenced with asshole lawyers, whose only formidable transgressions were having Type-A douchebag personalities, and the Dean who associated with ruthless crime bosses and dirty corporate giants, both domestic and international. The key to success was being the very best, which makes you irreplaceable, and Dean was, without question, the very best.</p><p>But being the best can only get you so far, and how much farther is Dean willing to go for Jake when the man comes tumbling back into his life, not to mend hurts once thought long forgotten, but to pull Dean into a tumultuous whirlwind of high-stakes political subterfuge and cut-throat crime rings dangerous enough to put them well over their heads...</p><p>Amongst warring corporate hounds and mafioso syndicates, Dean finds himself struggling with love, loss, family, and, most of all, what it means to truly be home for the first time in his life...</p>
            </blockquote>





	1. Chapter 1

Dean was sitting in a quiet corner of a dim bar, the smell of cigarette smoke, strong alcohol, and the worn hint of varnished oak permeating his senses; it was a small bar, tucked away in a less than desirable part of town, it’s patrons questionable to say the least, but only in the way that such bars make them out to be; all in all they were a mostly harmless group of your average wayward folk …modern nomads in the form of biker gangs, the occasional bunch of rowdy vagabonds with fake IDs, the jovially morose regulars who seemed to be nailed to the tables and counters, as if their chairs and glasses had their names on them…and the bartender, classically, was the keeper of many secrets with the key to exoneration ready at hand, and all you had to do was pick your poison. 

It was well worn in all regards and left its clientele with a warmth that settled deep in the gut, and not just because of the liquor; to Dean, it was homey, reminiscent of his childhood out in the great Northwest where the forests grew tall and thick…a dark, cool sea of thriving ponderosa pines and redwood sequoias, and where the smell of the air was so fresh it was heady; the fleeting memory of a rushing river, sinewy and thin as a whip as it carved its way into silvery gray granite, with its banks held back precariously by thousands of spidery roots bearing the fruit of ancient ferns and the crawl of yellow moss… it was enough to make Dean desperately yearn for home, like a tangible sickness laying hold of him. 

However, there was more to home than the superlative wildlife, and the rest of it Dean never wanted to see again; even now, in the bar, he sometimes caught himself remembering a painful memory sparked by the most ordinary of things: the distinct profile of a stranger, the occasional sharp crack of a glass set down too hard, the air tinged with whiskey… The worst was when he could sometimes swear he smelled the worn leather of his father’s jacket, the one that seemed as ancient as time, as a part of the old man as his God-given arms and legs. Sure, lots of people wore leather around here, he, himself, owned a leather jacket, but there was that _smell_ that was his father’s alone…

Despite the intermittent painful recollection here and there, and he would swear they really were few and far in between, this particular bar had become one of Dean’s favorite haunts; he loved the way this place was tucked away so nice and carefully, a true oddity in the big Windy City where Dean now called home. This haven was like an island by itself here, the only tribute to its physical location came from the ancient jukebox sitting by the door where blues and jazz bled from it, heavy and sultry and so damn good. He would sit silently, leisurely consuming one beer after another, watching people come and go, occasionally keeping score of the Bears games always blaring from a dinosaur-of-a-TV at the corner of the bar counter… If he was feeling particularly ambitious, he would sometimes rent a room at the seedy hotel down the block and charm a pretty damsel into his bed for the night, effortlessly, of course. 

Now, it was crucially imperative that this world he enjoyed here in the hidden parts of Chicago’s underbelly remain separate from his every-day world, the world where, by day, he was a reputable, expensive paralegal who wore finely tailored suites and ties and drank Starbucks on his way to work in the latest Chevy Impala LTZ. He went to modern bars and clubs that were decked in lots of glass and light and furniture he wasn’t sure he could sit on; he drank sparkling beverages that were sorry excuses for alcohol, and was always surrounded by a foray of successful friends sporting the brainchildren of Ralph Lauren, Jimmy Choo, and Versace. 

He spent his days working for one of the most powerful law firms in the city; his mornings and afternoons were passed in courthouses or skyscrapers and his evenings in a spacious, contemporary apartment overlooking the Chicago River and a bit of Wolf Point with his lumbering, giant dog Rosco; he had everything he ever could have possibly dreamed of, or so he thought most of the time… There was no doubt that he had come a long way from the tiny Washington town of his birth, and the ambitious, influential man he had created here in the heart of Chicago was everything he had wanted to be… 

There were two things Dean was very sure about: he would never be his father, and he was damn good at his job.

But being an exceptional paralegal was hardly his only profession… There was a part of himself that he had had to reconcile with a long time ago, and it was that he was a criminal at heart. Besides the honest hard work he put into assisting lawyers and hashing out paperwork for court cases (as honest as any of that can be…), he made a substantial living doing “odds and ends” for questionable people who had enough money to pay; he provided legal advice, as illegal as it may be, wrote up the occasional sub rosa contract or two, and often collaborated with others on projects, such as smuggling things in and out of the country, negotiating indentures with powerful clientele, and arranging the necessary drop here or there, amongst other things. 

He was good at these illicit games, and the fact that he was a _fucking_ paralegal made playing in the lion’s den all that more appealing to him, it gave him a rush like no other; besides, he was extremely good at covering his tracks and he had more aliases than James Bond, but, if anything were to ever get traced back to him, who was going to believe the squeaky-clean Dean Winchester was at fault? There were plenty of sordid little legal-wannabies who were much less careful and who could easily be pinned with the blame. Dean made sure of it.

And, so, the Dean sitting in the smoky, dark bar in ripped jeans and faded black T-shirt was very different from the Dean sitting in his twenty-second-floor office in a flattering gray suit and black tie. It was much like the difference between the Dean that conferenced with asshole lawyers, whose only formidable transgressions were having Type-A douchebag personalities, and the Dean who associated with ruthless crime bosses and dirty corporate giants, both domestic and international. The key to success was being the very best, which makes you irreplaceable, and Dean was, without question, the best. 

But he was also smart, and he made it very difficult for potential customers to come by his services, thereby successfully weeding out those he would otherwise never waste his time on. He was efficient and shrewd, to the extreme. However, you don’t get where you are all on your very own; just like most other professions, it’s networking that gets you places; it’s who you know and how you use their resources. His closest confidant, colleague, and the one bona fide family-friend Dean ever completely trusted was Bobby Singer, and between the two of them, they were a force to be reckoned with; while Dean put more stock in his day-job, out of necessity, Bobby was legitimately in the underground, making a modest living someplace out in the middle of nowhere but always in the right places at the right time (but never lingering long); he could rock a sleek suit when he needed to or run in the grittiest of crime rings, disguised and unheeded; he was a jack-of-all-trades, uncannily good at it all. If something big was going down, you could be sure to find Bobby somewhere in it.

It could even be said that Dean was in this life because of Bobby, or in part at least; despite the bad blood tainting Dean’s family, he would begrudgingly give his father one thing: like Bobby, like Dean, John Winchester had been the best at what he did too, and it was all Dean could remember even from his earliest childhood memories, the way he knew, deep in his gut, his father was a criminal, but not in the crude sense of the word… He was a fine and rare Macallan whiskey compared to the bottom-shelf moonshine working out there. John Winchester had been top dog, but also unforgivably ruthless…and it had been his undoing. Now, Dean was caught up in the same business, the “family” business you could say, and he loved it and hated it all at once; he could be perfectly happy being a successful paralegal, he could make a perfectly reliable, reputable living that way, and as far as almost everyone in his life knew, he did, but it wasn’t enough and it would never be; he knew this for a fact. He wanted to play the dangerous game, was addicted to it like a drug, knew he needed it just like his father did before him, cursed with the ever-seeking thrill of living two lives, conspiring to make economy-sized dominoes fall, covering up his tracks so good it was almost tempting to intentionally let something slip just for fun…

But Dean was better than his father had ever been, and even though they shared this monstrously huge infatuation with breaking the law, Dean would swear vehemently that he was not like his father and never would be; he was a stronger man than his father and a superior contender on the lawless chessboard that was their lives.


	2. Chapter 2

He was about to call it a night and take the CTA blue line back up town when he felt his phone vibrate in his pocket; this would normally never be alarming in and of itself, except that it was the cell phone that hardly ever rang; it rang in case of emergency, and that was it. He first touched his every-day iPhone deep in his pant’s pocket to make sure he wasn’t just imagining things, but it wasn’t the iPhone. As if a switch had been flipped in his brain, Dean went from paralegal mode to barely legal mode and fished the Blackberry from the inside pocket of his jacket. Most of the incoming calls had been from Bobby over the years, and it had never really been good news when Bobby called this particular line. The caller ID he didn’t recognize, but that wasn’t all too unusual; when he answered it, however, he knew in an instant it wasn’t Bobby. 

“Evan Fischer?” The voice asked, and it was steady, sure, and oh-so-familiar. Dean felt his knuckles go white around the phone, utter surprise stopping him dead in his tracks. In his shock he was about to blurt _“Jake?”_ but his brain put the breaks on hard: Jake would know better than to assume “Evan Fischer” was anything but a false name; he wouldn’t call this number without knowing it was Dean who would answer… so the charade was intentional…why? Suspicion and an irksome worry curled its fingers around Dean’s insides, and he realized the silence on his end must have been going on forever,

“Yes?” He finally managed, his voice tight in his throat. Overriding the suspicion and worry was now a flood of anger. _You haven’t called me in over a year, you son-of-a-bitch. Why now?_  
The silence on the other end was strained, as if Jake could hear him thinking, 

“Can we meet up?” He finally managed, his voice now wavering slightly, the surety gone, “Strictly business.” He added quickly, leaving the air heavy with things unsaid. Dean felt his hand come up to press the pads of his fingers into his closed eyes, then letting them come down to squeeze the bridge of his nose…

“Do you remember the place where we first met?” He finally replied, the sudden weariness he was feeling slipping behind the mask of a cool, calculating, unreadable tone. The words themselves sounded strangely intimate, and Dean found himself distracted by wondering if Jake thought they were, but the response was equally stoic,

“Yeah. Meet me there tomorrow at nine?” Dean felt the conversation coming to a close and he found himself wanting to hang on to the way that voice was familiarly deep and gravely, to hang on to the millions of different ways he’s heard that voice before…

“Sure.” He answered, not trusting himself to say more. And the man on the other side hung up with a quiet click, leaving Dean with a ringing in his ears he couldn’t explain.

The rest of the night found Dean laying in bed, wide awake, wondering what could have caused Jake to call; he hadn’t heard from the man since a handful of jobs ago, now almost two years past, when they had been working together with Bobby on some job in Texas where some duly unnamed but valuable merchandise needed to be seamlessly run in from Mexico. Before that…they had worked on plenty of jobs together; Dean had considered Jake one of his best contacts. 

But more than that, there had been something else; in a nutshell, Dean had never been one to abide by the golden rule of never mixing business with pleasure.  


Things had gotten complicated, for complicated reasons, and for the past year and half, at least, Dean hadn’t heard from Jake and Jake hadn’t heard from Dean. They both knew, to some extent, that that was the way this game was played, everything was permeable and easily erased, replaced, or, worse, broken. A job had to function better than clockwork, it had to get done fast and clean, and, if it didn’t, it was only a matter of time before some part of it broke; when you’re dealing with merciless crime bosses and cut-throat CEOs, no matter how directly or indirectly, if something goes wrong, there’s a lot at stake, a lot to be lost…

So what could Jake have possibly done to have to call Dean? What kind of trouble could he have gotten himself into that he had to call “Evan Fischer” on an emergency line?

Dean rolled onto his side and watched the way the warm glow of city lights filtered in through the closed curtains and landed in bold stripes across the hardwood floor, the carpet, finally reaching him as it tapered over the bedspread and into his eyes, a dull ache forming behind his retinas; that was another thing: he missed home where nights were spent in complete darkness, uninterrupted and welcome. Here, you couldn’t escape the damn light, especially at night, but, out West, in his thousand-something hometown, it was blissfully dark, and if you really wanted to see some light, all you had to do was step outside and find the billions of stars shining clearly in the black velvet sky, or the moon, crisp and almost corporeal, not the occasional, filmy thing that hovered in the sky washed out with man-made illumination and tinged orange, hazy with smog.

Dean found himself remembering a particular job he and Jake worked many years back in the sweltering tropical heat of Belize where a prominent drug cartel and a wealthy American conglomerate were settling a tentative subsidiary agreement; said conglomerate had scooped Dean up for a high enough price, and Bobby had weaseled Jake into the operation as a legal informant through another contact, some high-stakes Latin financier keeping tabs on his investment. 

It had been a particularly unproblematic job, all things considered, but he remembered how the heat was so oppressive, even at night; the only relief came in the fleeting form of wind coming in from the Caribbean Sea. Dean distinctly remembered that the moment the job was finished, he and Jake escaped Belmopan as fast as they could to find a beach somewhere on the Gulf of Honduras…  


The stars on that beach were as bright as the ones in rainy, gray Washington, if not brighter. He remembered the feeling of the course sand between his toes, the smell of salt and the steamy tropics, the sound of the dark waves crashing on the shore like thunder…

“I fucking miss LA.” He remembers Jake saying, although not resentfully… it was just a gentle sigh, still content but yearning for familiarity. Even as Jake said it, he was walking into the surf, running his toes through the pearly foam left behind in its wake. Dean had laughed and spread his arms wide, feeling the damp stick of sweat make his thin T-shirt cling to the small of his back,

“What?” He followed Jake into the water, marveling at its warmth, “You don’t like paradise?” He jabbed, sarcasm thick in his tone. Jake turned to face him, his figure lit by the stars and the moon; his smile gleamed in the twilight, and Dean could barely make out the way he rolled his eyes,

“Oh yeah.” He chuckled, deep and genuine, “being sandwiched between the fucking Magaña family and some American jackass with too much money is a delight!” He snorted, “I’ll really hate for our vacation to end...” But when he turned back to face Dean, he found him with his gaze upturned to the sky, those lips parted ever so slightly in the kind of awe Jake doubted he allowed many people to see,

“Yeah,” Dean mumbled absently, and after a long moment, “Just fucking look at this, man…” Jake stepped closer and followed his gaze, and there, far above their heads, an intermittent but steady shower of meteors streaked the black sky with blazing white and gold.

“What the fuck?” Jake breathed, “Shooting stars? I’ve never seen so many in my life…” and Dean had laughed at him, although he couldn’t say he had ever seen as many before either…

In his Chicago apartment, with the lights that never faded and the city sounds that never waned, he could remember other things from that night… The feel of warm skin, muffled laughter…his name wrung so beautifully from those lips, slick with saliva…


	3. Chapter 3

He awoke abruptly to the harsh morning light, his dream slipping away like wisps of smoke, never to be fully recollected again. His sweat was already turning cold as he let the sheet slip down his naked torso, and he shivered. He scrubbed his hands over his face and groaned: waking up was difficult some days for reasons unknown to him. As he was contemplating how crucial coffee would be in the next couple of hours, he swung his legs out of bed, got up, and found he was ridiculously hard. He cursed under his breath, wondering again about the damn dream that was so elusive now, although he had little doubt what it might have been about…A familiar face swam into his mind’s eye and he wanted to punch a fucking wall. Instead, he headed for the shower, determined to think only with his upstairs brain.

When Dean got off the elevator that morning, he stopped by Roy Branson’s office to drop some documents off and share some mutual bitching about last night’s bad game between the Cowboys and the Saints; Roy was a decent guy, as decent as a lawyer could be, and maybe that wasn’t saying a lot, but Dean liked him for the most part and they got along just fine. The two of them had been working on a case together and were about done finishing up with the last of the legal proceedings, tying up all the loose ends and the like; it had been a bitterly drawn out but otherwise mundane-as-fuck divorce case that had driven the both of them absolutely crazy; Dean was sick and tired of helping Roy redraw up the settlement at the Mr. and Mrs.’ every resentful whim. Dean was more than happy it was coming to a close, that was for sure.  
Dean was about to leave when Roy shouted after him,

“Hey! You want go out with Carter, Dawson, and a few of the other guys tonight, grab some drinks?” Dean was about to throw a smarmy remark about demanding to be exempt from babysitting lawyers drunk-off-their-asses before accepting the invitation, but his mouth snapped back shut before he could say anything. He shook his head with an apologetic smile,

“Sorry, man, wish I could,” He waved a file in Roy’s direction, and shrugged, “Got plans.” Roy grinned, leaned way back in his chair and made to toss a crumpled piece of paper into the waste bin across the room,

“Plans, huh?” He whistled suggestively and Dean looked both ways down the hall before giving Roy the bird, “What kinda plans, Casa Nova? Gonna get lucky tonight?” He sing-songed, crumpling up another piece of paper off his desk and making to throw it at Dean, who stood in the doorway,

“Say what you want, Branson. At least I can get some.” He easily dodged the piece of paper, and turned to leave, laughing as he went, “Not my fault if you can’t.”  
As he strode to his office not too far away he was met by his pretty blonde assistant, Jo Harvelle, who had one of those ‘looks’ on her face,

“ _Really_ , you guys,” She started, picking up the ball of paper that had bounced out into the hallway; she was trying to look serious, but a grin was cracking at the corners of her lips, “You’re supposed to be respectable, hot-shot professionals, and you’re acting like prepubescent school boys,” Dean chuckled and nudged her shoulder as they exchanged some files and Jo handed him a steaming cup of coffee, just the way he liked it,

“I didn’t know my mother was interning here,” He ribbed and she rolled her eyes, “Besides,” he added, making his way into his brightly lit office, “If you knew what we were talking about, you wouldn’t describe us as prepubescent boys, hint, hint.” And he winked at her with a most disarming smile, but she didn’t falter or even blush; she blew out a frustrated sigh and rested a well-manicured hand on her hip,

“Mr. Winchester,” She warned, lips still quirked in a smile, “If that's the case, you don’t want to know how I would’ve described you two.” He had to admit, he loved goading her at times; she was such a good sport,

“Egotistical dirty bastards?” Dean supplied, sipping his coffee,

“To put it mildly,” She smirked, and Dean put on an exaggerated show of bowing down over his desk in mock submission,

“Well, thank you for sparing me your harsh words, your highness.” She grinned in achievement, before giving him another signature eye roll and plopping some mail down on his desk,

“Why, of course, Mr. Winchester. You are, after all, my favorite subject.” She drawled; she then sifted through some of the letters and pulled one out, switching from pretty and clever to serious and efficient in the span of a breath, and she made it look as smooth as silk, “Don’t forget about the meeting with Mr. Bates and Mr. Johnson at two, and this letter is from a…” She looked closely at the company logo on the front, “…a Mr. Crowley. From LCC.” She set the letter on top of the others and missed the way Dean’s relaxed and comfortable features morphed into something angry and distrustful in the blink of an eye. When she looked up, the look on his face was gone, replaced once again by his attractive smile and warm eyes,

“Thank you, Ms. Harvelle.” He said, and Jo knew from his ever-so-slightly strained and distracted tone that he was strictly business now; she knew from that tone that he had work to do. She nodded, smiling, and flipped quickly through her day planner,

“And you have a lunch meeting with Mr. Devereaux at twelve-thirty, don’t forget that.” Dean was sitting now, his elbow resting heavily on the desktop and his fist pressed gently against his mouth, which was set in a grim line, his eyes met Jo’s for a brief moment and his lips turned up in a smile. He really was thankful for her help; she was always sharp when he needed her to be,

“Thanks, Jo.” He said quietly, and, as if a switch had been flipped, he was back to his snarky ways, “What would I do without you?” He teased, and she pretended to throw her pen at him before tucking it into the spiral spine of her planner,

“You’d be in a ditch somewhere, I imagine.” She joked over her shoulder as she headed out of his office, her heels clicking on the floor. She shut the door to his office softly, and Dean was plunged into sudden silence. He sat at his desk, his eyes lingering on the letter from Crowley, as if he could burn holes through it. He sighed heavily and fished out his Blackberry before getting up to pace in front of the floor-length windows that overlooked the crowded, gray city from twenty-two stories up.

Bobby picked up on the second ring,

“Well, if it aint my favorite hoity-toity. I bet you’re feelin’ like you’ve got a stick up your ass in that God-awful suit you’re wearing right about now.” He listened to Bobby rummage around that beat-up, run-down, lived-in-for-God-knows-how-many-years house of his, and when he heard Bobby swig something with an audible sigh of contentment he was pretty sure it could only be one of two things: coffee or alcohol. And he was pretty sure it was the latter. “How’s that big-ass city of yours, huh? Still gottcha by the balls? I tell ya, Dean, when are you going to be coming out here? When’s the last time you actually saw a damn tree? Or walked through a patch of grass bigger than a fucking square foot, man?” Dean couldn’t help but chuckle; it had been a while since he’d talked to Bobby, and he’d forgotten how endearing and maddeningly frustrating he was,

“Hey, old man, I didn’t call in order to listen to your running commentary,” He chided, “and, for your information, Chicago’s got plenty of trees.” He could hear Bobby snort and mumble something inaudible,

“The hell it does! I’m ashamed you’d even say such a thing, you idjit. You know what a damn tree is, and there certainly aint any _there_.” He scoffed. Dean had to concede; Chicago might have trees, but the scraggly things lining the cramped concrete jungle down there were hardly anything compared to the monstrous, towering creatures out in the forests he used to be so familiar with.

“Got me there,” He sighed, and he could tell Bobby had straightened up a bit at the tone of his voice, like he could instantaneously tell something was off.

“What’s up?” Bobby finally asked, his voice gruff, ready to weather a million different things if it came to it. Dean pinched the bridge of his nose and squeezed his eyes shut; it had been something he’d found himself doing more often these days,

“…It’s nothing bad,” He started, although he realized his voice was probably not that assuring,

“Not bad.” Bobby echoed, “Okay. Well that can mean anything from…not being on somebody’s hit-list to…not going to jail…” Dean let out an abrupt laugh,

“Well it’s none of those things. So it’s really nothing bad.”

“Well, boy, then what the fuck is it?” He barked, “I know you don’t call just to hear my lovely voice.” The both of them had to be grinning at this, and even though Dean couldn’t see Bobby through the phone, he was sure he was. The smiles didn’t last long though.

“Truth is, I’m not sure what it is yet. But I got a call from Jake last night,” He started, and Bobby was painfully quiet, “Sounds like he might’ve gotten himself into some shit…” and he could hear Bobby let out a long breath. The line was quiet for a long time.

“I haven’t heard anything from him.” Bobby finally said, “He hasn’t contacted me.” Dean wasn’t sure if he should feel better knowing this or not, but at least it answered one of the questions he'd been wanting to ask,

“So you don’t know anything about it…?” Dean hazarded. Bobby let out a negatory grunt,

“I haven’t heard a thing. You know it’s bad though if he’s…” Bobby trailed off. _What? Calling me?_ Dean wanted to demand, but he stayed quiet; it wasn’t about that. 

“You know it’s bad if he’s calling for help, is the thing.” Bobby finally finished, his voice devoid of any revealing emotion.

“ _Everyone_ needs help sometimes,” Dean snapped, before he could reign in his reaction.

“I’m just saying.” Bobby replied, his tone a bit terse, “He’s a big boy. He’s more than capable of handling his own shit.” Dean couldn’t help but lean his forehead against the cold glass, although he would regret it: he hated those damn smears that were left behind, worse than nails on a chalkboard. But the glass was cool, and Dean felt like he was overheating with anger, mixed with regret and something else…fear? Bobby was saying something else, his voice grounded, just what Dean needed,

“…You’re meeting up, I take it?”

“Yeah. Tonight.” Dean replied, “I’ll call you when I know more…I just…” He paused for a long moment, before peeling himself away from the window; he strode to his desk and picked up the letter from Crowley.

“What is it?” Bobby asked, his voice clipped...or anxious, if Dean didn’t know any better, but there’s no way he’d ever say it to Bobby; Bobby would just tell him to go to hell.

“I got a letter today from fucking Crowley.” Dean spat, turning the letter over in his hands as if he could somehow will the letter to disappear. Bobby was deathly quiet on his end for more than a good minute,

“Well?” Bobby finally demanded. Dean threw down the letter and rolled his eyes,

“Well, I haven’t opened it yet!” He hissed but lost his steam in the same instant. He seemed hesitant before mumbling, half joking, “I’m kinda fucking scared of what’s inside, y’know…” He hoped maybe it was too low for Bobby to hear, but, of course, he was wrong,

“Letters don’t bite, you damn moron! Open it!” If Dean weren’t more annoyed than he was amused, he’d laugh, but before Bobby could get any reaction, Jo buzzed him,

“Mr. Devereaux is here, Mr. Winchester.” Her voice was a bit scratchy through the intercom, but clear enough to drag him away from the prospect of opening the letter, thankfully.

“I gotta go. I’ll call you back when I know more on both fronts.” Dean promised,

“Yeah, yeah, _Mr. Winchester_.” He mimicked Jo’s voice at the end, high pitched and womanly.

“Wow, Bobby. I’m pretty impressed. Have you been working on that?” Dean said sarcastically between paging Jo back that he’d be out in a minute. He could hear the older man laugh and curse under his breath at the same time,

“Just for you, sweetheart. Now get on a fucking roll!” And with that, the line went dead. Dean gave one last laugh as he jammed the phone back into his pocket and went to meet Devereaux who was waiting outside his office. 

 

* * *

They were sitting out on a veranda overlooking the city, which was spotty behind thick swaths of misty fog; it had been an all around gray day, but Frank had insisted that they sit outside where “no one could hear them.” Dean suspected the culprits, who remained unsaid, could’ve been anyone…the seedy software corporation Frank currently worked for, Dean’s legal firm, the government, the Russians, Al Qaeda, or aliens. Frank was certainly unorthodox, and when they had stepped outside onto the patio Dean was about ready to tell Frank to shove his aliens where the sun doesn’t shine: it’s fucking cold in Chicago this time of year, and he didn’t care who was listening to them if it meant he could enjoy his lunch inside where it was preferably twenty degrees warmer. But Dean knew better than to cross Frank who would clam up good if he felt encroached on; so here they sat, their napkins blowing in the occasional icy breeze, Dean’s hot coffee a blessing between his fingers.

Frank lit up a cigarette and took a long drag, his eyes squinting over at Dean through his thick-rimmed glasses; Dean waited patiently for Frank to warm himself up and get the conversation going, as he had learned the hard way to do. Frank could never be pressured into saying or doing anything before he was damn well ready to, and this frustrated Dean to absolutely no end, but he had been smart enough to realize there was very little he could do about it. Frank cleared his throat and flicked some of the ash of his cigarette over the side of the balcony, where it swirled away in the wind.

“So,” He started, a wry smile appearing on his lips, “How’ve you been, princess?” And Dean barked out a laugh, all the while thinking how nice it would be to snub out the man’s cigarette in his eye.

“Spectacular. Living the royal life one day at a time.” He assured, smirking. Frank nodded sagely and sipped his coffee,

“Still working with those damned lawyers?” Adding in a bitter huff, “sons-of-bitches.”

“Have to earn the bread and butter, right?”

“So more like life’s a royal pain-in-the-ass then?” Frank corrected, an deep chuckle rumbling from him. Dean tilted his head in amused agreement,

“Well, if you can’t beat ‘em, join ‘em.” Dean supplied, and Frank gave him a devilish, knowing grin,

“And _then_ beat 'em.” He finished and Dean raised his coffee in appreciation.

At this time, the waiter decided to carry out their orders, and there followed a long comfortable silence in which they sat eating their lunches and watching the sluggish churn of the wide river run below them, murky and gunmetal gray.

Frank wiped his mouth with his napkin, placed it beside his empty plate, and looked at Dean curiously; it was a look Dean had rarely seen, but he knew what it meant.

“You take any jobs lately?” Frank made no pretenses; it was one of his most consistent qualities. Dean gave him an unreadable look, calculating the weight of all the possible ways he could answer that question. It wasn’t a matter of whether or not Frank knew about Dean’s penchant for the prohibited; on the contrary, Frank was one of the most highly and uniquely skilled operates Dean knew, and, not only that, but he also considered the man a close associate who could, above all else, be trusted. Those were the ones who were few and far in between. The truth was, no, Dean hadn’t been working any jobs recently, at least, not ones that made for particularly significant discussion.

“I suppose I’ve been on a bit of a vacation...” He joked, and Frank grumbled, setting his lips in that firm line he usually adopted when he was torn between laughing his ass off and being annoyingly severe.

“Vacation, Dean? You shit.” He said, glaring at Dean pointedly, but a thin smile wasn't quite hidden behind his lips, giving him away, “Next thing you’ll tell me is you’ve abandoned us all for the moral high ground, right?” Dean burst into laughter,

“Ha ha! Hardly.” He shook his head, still chuckling, “Forget the moral high ground. I’m afraid you’re stuck with me.” Frank made a grand, exaggerated show of being disappointed at this news, to which effect Dean told him he could fuck off.

“What about you, Frank?” Dean finally asked after more taunting banter, “I’m sure you’ve got plenty of fans waiting in line, huh?” Frank raised his eyebrows and inclined his head in a little nod, but the amused smirk on his face hardly reached his eyes. Frank didn’t answer right away, instead opting to light up another cigarette. Dean watched the flame of Frank’s lighter flicker in the breeze; his gut was slowly telling him some transition was happening, and he wasn’t sure it was going to be good. Frank tucked the lighter away and leaned forward on his elbows, his look alarmingly serious,

“No jobs for me,” He started, voice low, “Not now anyway.” And his features were grim and rigid. Dean gritted his teeth, a million questions wanting to slip from his lips,

“You didn’t just come here to have a nice little lunch with me then, did you, Frank?” Dean asked, and it was really less of a question than a certain segue into the things left unknown. Frank gave him a brief smile,

“As if I ever do, you twat.” The jab was short-lived; Frank shook his head slowly, as if weighing his words,

“You know I keep my ears to the ground...” and Dean definitely knew this; the old man was fucking paranoid as all get out. This was another quality Frank could easily be relied upon for, and it had come in handy more than a couple times. When Frank started a conversation with those words though, it set Dean’s nerves on edge and made the hairs on the back of his neck stand up. All he could think to himself was, _Shit shit shit_.

“I’ve come across a few tidbits here and there…” He shook his head in frustration, and when it made no sense to Frank, it sure as hell made no sense to anyone else; there wasn’t a whole lot more frightening than that,

“Well what the hell is it, Frank?” Dean demanded; he hated waiting, especially when it felt like a completely unsuspected bomb could be dropped on his head at any moment. Frank licked his lips, and leaned farther over the table,

“Are you familiar with SucroCorp?” Frank asked, his voice quiet. Dean scrunched his nose in confusion,

“Sure. It’s a subsidiary of…what…Richard Roman Enterprises, right?” Frank nodded enthusiastically, that half-crazed glint in his eye coming on.

“Exactly. Fucking Dick Roman.” He looked absolutely livid now, “…always knew the bastard was a piece of work…When all goes to shit, at least I can say ‘I told you so’; the guy’s a fucking whack job…” he began to rant, and Dean wrapped his knuckles against the tabletop, riveted with the implications of where this was going,

“Wait, wait, Frank! Get back on the train, man. What’s going down with Roman?” Frank blew air out through his teeth in a huff, running his hand through his already disheveled graying hair,

“That’s just it!” He seethed, “I’m not sure! But something is definitely happening, Dean. Something big.”

“Well, just tell me what you know,” Dean suggested, apprehension tightening in the pit of his stomach.

“For starters, SucroCorp is expanding.” Frank let out a mirthless, harsh laugh, “And that should be fucking scary enough, but that’s not it!” He drummed his fingers on his knee, restless, “It’s _how_ they’re expanding.” He leaned forward again, eyes sharp as they bore into Dean,

“I first noticed a couple months ago some shit was getting picked up on my radars, y’know…” He waved his hand in irritation; explaining these things was a bitch, 

“First it was just random, but then I started to notice a trend…somebody was buying up a shit ton of businesses and land.” Dean shook his head in frustration,

“Wait! You keep track of that stuff? How?” Dean should’ve known better than to ask something like that. The answer was always clear:

“I keep track of _everything_ , dumbass!” Frank retorted, obviously annoyed by such an insignificant detour. Dean nodded in easy consent; that Frank definitely did do. 

“I’ve got programs that keep tabs on things, got it? Stock exchange, housing market, you name it… I run these algorithms—” Dean held up his hands in defeat and cut him off,

“Yeah. Got me at the jargon. Keep going…” Frank gave him a dirty look, and Dean knew what he would’ve said if given the chance: “Dean, you ape, this is child’s play. It would do you some good to know how to do some of this shit.” To which Dean would gallantly reply, “That’s what I’ve got you for, Devereaux.” It was a recurring theme in their conversations, to say the least.

“Anyway, jackass, so all this real estate gets bought up, and all of a sudden I realize why it’s so damn bizarre: it’s Dick Roman!” Frank has to light up another cigarette before he can continue, “But!” He stabs his cigarette in Dean’s direction, “That’s hardly the kicker. He’s snatching these huge parcels of industrial wasteland out in the middle of fucking nowhere...” Dean waits for him to continue, and when he doesn’t, Dean feels about ready to explode,

“ _And?_ ” He snaps.

“ _And_ guess who used to own that land.” Frank snipped back, smugly, clearly proud of himself for whatever he happened to find out. Dean was having none of it though,

“How the fuck should I know! Who?”

“LCC.”

It took a moment for the reality of Frank’s statement to sink in. Dean sat back heavily in his chair and was deathly silent as his brain raced to catch up with the rest of the situation.

“ _Crowley…_ ” He finally muttered. Still, this answered practically nothing. If anything, all of this just made more questions. He stared over at Frank, incredulous,

A weak “So…?” was all Dean could manage. Frank shook his head sadly and shrugged,

“That’s all I’ve got, kid.” He blew out a waft of smoke, “I wish I had more. I'll be damned if I'm not laying low for now, though… Everyone knows those two don’t play nice, so why they’re suddenly buddy-buddy is enough of a cue for me.” Dean couldn’t shake the way Crowley’s letter, which still sat unopened in his office, was now ten times as unnerving as it had been this morning.

“I’m sure whatever they’re up to, we’ll be able to steer clear.” He said, but he didn’t sound as sure as he would’ve liked. It was true, though, that those huge conglomerates would probably have very little use for the likes of them, although both Frank and Dean had done work with one or the other at some point in the past. Dean had never worked for Roman before, and he knew from gossip on the grapevine that he wouldn’t likely want to, but he’d had some dealings with Crowley, whose innate nature seemed to be entirely two-faced and a hell of a lot slipperier than Dean preferred.

Frank gave a small sigh, “I know I’m not taking any chances. I imagine, with expansion like that, Roman will be looking to have some dirty work done; they usually always do, especially his type.” Dean couldn’t say he disagreed.

“Well keep me in the loop if you find out more, alright?” Dean said, getting up from his seat and automatically smoothing down his tie. Frank looked tired as he gazed up at Dean from his chair; there hadn’t been a time when Dean thought a look like that was possible, and he wondered if there might be more Frank wasn’t telling him. At that moment, Dean felt suspicion creep up his spine, his better judgment scrutinizing the situation with sudden clarity,

“What else is there, Frank?” And his tone left no room for bullshit. Frank scratched his temple and averted his eyes, squinting over the balcony and into the stormy horizon.

“...So maybe I dug a little deeper than I should have,” He still wouldn’t meet Dean’s eyes, “Looks like some important documents were swiped right from under Roman’s nose… I might’ve hacked a couple emails detailing the urgency with which these papers must be retrieved…” Dean opened his mouth to interject, but Frank shut him up with one look, “ _Don’t_ ask me what the documents are. I don’t know. But I _do_ know _who_ has them.” He sighed heavily and continued, his words halting, “It was a David Larson.”

Dean felt like the floor had been ripped out from under him; the shock stunned him into a silence he wasn’t even sure his own thoughts could penetrate. _David Larson…But that’s…_

“The thing is…” Frank started up again, abruptly and uncomfortably, “If _I_ know who did it…it means Dick Roman does too, and I’m thinking it’s not as important to _retrieve_ these documents as it is to _eliminate_ them, if you get my meaning…” Dean had no way to respond; he was still dumbstruck as the pieces slowly started to click together in his mind. Frank was about to suggest Dean take a seat again, but in that same moment Dean seemed to snap back to reality, his features schooled into an unreadable expression.

“That’s a twist…” He said, his voice giving nothing away, “Thanks for letting me know, Frank.” Frank stood up slowly from his chair and held out his hand to Dean, who shook it absently.

“Of course, kid. No problem. Just…lay low for a while, okay? Don’t do anything I wouldn’t do.” The two shared a short laugh at this, and Dean nodded gratefully, coming to his senses a bit more.

“No promises there, but I’ll see what I can do.” He replied, “Let me know if you come up with more.”

“I will. And you know how to get a hold of me, if you need to.” Frank leaned in, his eyes painfully grim, “Seriously. Get out of town. Stay off the radar.”

Dean said he would, but he was sure there was no way he could possibly mean it.

**Notes for the Chapter:**

> So I kept the name SucroCorp, but it will maybe or maybe not follow canon. I'm thinking there will be some elements that remain the same, but, on the whole, please think of it as an entirely different entity than the one on the show. Much thanks!


	4. Chapter 4

When Dean got back to his office, he couldn’t bring himself to open Crowley’s letter. Not before he met up with Jake and figured out what the hell was going on; any more surprises in one day and Dean was sure he would have a fucking heart attack. And the meeting with Jake was just about all Dean could bring himself to think about; the ever-present reality of seeing Jake after so long loomed in the back of his mind like a constant black shadow. It wasn’t bad that they would be seeing each other, he kept trying to reassure himself, just irritating on so many levels, like the frustrating sting of a wound reopening. Still, he couldn’t deny the small part of him that desperately wanted to be in the same room as the other man, to feel that keen connection with another human being who, at one point and time, had known him so well.

He found himself remembering the first time they’d met; it had been maybe close to ten years ago now. There was some speculation that it might have been longer than that as both of them had served in the military when they were much younger; and, while they hadn’t served together, their units had shared the same post in Afghanistan for a while and there was a good chance they may have run into each other at some point. They had laughed over this possibility countless times, but now Dean could only wish there had been solid evidence that they really had; he would never admit it, even to himself, but it would mean there was more for him to hang on to.

Their first job together had occurred at a time when Dean was finishing up his certification at Loyola University while working as a legal assistant and dating a woman named Danielle Harrisburg, who was an ambitious and stunningly beautiful up-and-coming lawyer. Apart from a rapidly successful climb to paralegal stardom, Dean had also been busy making leaps and bounds establishing himself as the go-to-guy for unfailing, discreet, and proficient service in all things unlawful. 

Dean had no trouble carefully fabricating some vague and easily defendable “family affair” that would let him escape his plans and obligations with both his girlfriend and with work in order to do the job Bobby had roped him into. He was supposed to collaborate with a liaison that had been working to obtain some incriminating information on some CEO’s business practices and Dean was supposed to conjure up some legal papers in turn; the papers would change hands appropriately and some company somewhere or other would then crumble into oblivion. The job wasn’t supposed to be particularly difficult, and it wasn’t, but what consequently came of it would change Dean’s life forever after. 

On Bobby’s direction, Dean went to the airport to pick up one David Larson who would be flying in from a layover in Frankfurt. When passengers started filing out from customs, a man, probably close to Dean’s own age, if not a bit younger, strode out wearing a nicely tailored black suit. The man easily fell into step with Dean, who knew better than to start making conversation right outside a busy terminal, especially considering the nature of their occupations. Dean occasionally tried to study his new business partner when he could catch a glance: the other man’s hands were casually tucked into his pants pockets and his posture was remarkably comfortable and relaxed. They were about the same height, but Dean was a tad bit broader in the shoulders whereas this David Larson was muscled, but lean, resembling that of a swimmer’s body. He had dirty-blonde hair that was highlighted with the result of too much sun. It was casually swept back in a genteel fashion, but Dean suspected it was to properly complement the formal attire; he could imagine it ruffled and falling into the man’s eyes on any other average day. Speaking of eyes, his were a vivid chestnut brown, warm and tinged with gold when the light caught them just right. Dean wasn’t in the habit of admitting it when a man was particularly good-looking, especially not when they were business associates, but he had to admit that this Mr. Larson was striking in a way he found hard to ignore.  
“Welcome to Chicago, Mr. Larson.” Dean had said with a wry smile as they walked to the baggage claim to collect the man’s single duffel bag, “It’s a good thing you’re not planning on staying long, the weather’s fucking terrible this time of year.” Larson let out a deep laugh, his voice as smooth as the way he easily moved to swipe his bag up off the conveyor belt.

“I have to admit, I’m not happy about spending the rest of this damn job in the rain; it’s a bad joke compared to the weeks I got to spend in Spain.” He said sheepishly. So that would explain the sun-bleached hair and the even tan. Larson turned to Dean with a smile almost as beguiling as his own, and Dean couldn’t help but smile back, like it was infectious.

“As nice as it was though, I’m so fucking glad to be back in the States.” Larson admitted, and Dean watched, fascinated, as a slow transformation occurred: Larson eventually took off his tie, tossing it into his bag, and casually unbuttoned the top of his dress shirt. The conversation felt frighteningly natural, and before Dean knew what was happening he found they had made their way into one of those airport restaurants, a steakhouse decently outfitted with a sports bar and flat screen TVs, booths with coffee-colored upholstery and dark wooden tables and chairs; the lighting was subdued in the way that many steakhouses are and the waiters all wore tasteful black button-down shirts.

Larson was going on about how he missed having a proper steak and how a month in Europe had made him hopelessly yearn for hamburgers and French fries and other unparalleled staples of American living. Dean couldn’t agree with him more, having spent some time here and there abroad; and, while he had quite an affinity for traveling, he knew there was nothing quite like the relief and appreciation felt when touching down in the country of your birth. Besides, you really couldn’t go wrong with a respectable burger with all the trimmings—and pie! Nothing could beat a good old apple pie.

They had sat well into the evening drinking Budweiser and eating expensive rib-eye. Dean appreciated the gradual conversion he saw take place in Larson, who wore his fitted dress shirt—presently rolled up to the elbows, further unbuttoned at the top, and slightly wrinkled—just as well as the pressed, immaculate suit he’d come off the plane with. His hair was also disheveled now, but, if anything, it only made him look a bit younger, and Dean was sure most would pay a lot of money to have their hair look like that. Their banter had been effortless, and Dean couldn’t help but feel that he’d fallen for that cliché where they’d known each other for years instead of actually being perfect strangers. Dean found out that the other man was an avid football fan, as he himself was, and that, while he enjoyed his fair share of soccer, he’d nearly been dying with too much of it overseas, and there was hardly a proper pigskin to be found anywhere. He learned that Larson had gone to UCLA and was happy to find a kindred spirit who appreciated the West coast as much as he did; Larson had grown up on the sunny beaches of California, and he desperately missed it. He currently lived in and worked out of LA, although he hardly had much of a chance to get home most of the time. Dean felt the strange desire to divulge a bit about himself, so he lied and told Larson he had been born in Ashland, Oregon, and that he’d only spent a short period of his childhood there; talking with someone he hardly knew about home and growing up wasn’t a good idea for many different reasons, mostly professional, but the biggest reason was that Dean was very secretive of a childhood he felt compelled to erase. Telling someone he had been born in Ashland, Oregon, was as close as he’d ever gotten to the truth about Roslyn, Washington, geographically speaking anyway. Something about this man made Dean want to spill his guts all over the floor, and the feeling was certainly unnerving, to say the least.

That same night, when Dean dropped the man off at his hotel, Larson still had that charming, confident smile on his lips,

“Thanks for humoring me back there, man. I was seriously starving for some American grub. I think if I had to eat one more piece of Brie or another bite of caviar I was gonna be fucking sick.” He laughed, his voice deep and genuine. Dean shook his hand and quirked his head to the side in a short nod,

“I feel you, man. No shame in a good steak.” He assured, and watched as Larson hoisted his large duffel bag onto his shoulder. There was a split second where they studied each other carefully, disregarding any notion that it might turn awkward; before too long, another small smile spread over Larson’s face and he stepped forward slightly, confidentially,

“You’re a good guy. Glad to be working with you on this.” He said, shrugging casually as if it would help dispel the electric tension hanging in the air, “So I think a proper introduction’s in order,” He held out his hand again, 

“My name’s Jacob Royer, but call me Jake.”


	5. Chapter 5

It had been several hours since the sun set by the time Dean left the office, and, although it was dark, the sky was tinged orange and hazy with city lights; the night-time chill that ran up his spine when he stepped out of the building was proof enough that winter was well on its way, and he hated it. He shivered his way into his car and cranked up the heat, yanked off his tie, wrestled out of his uncomfortable suit jacket, and finally shot out of the parking garage and into downtown. He was running late, which was something he never did, but Jo had caught him at the last second with some more paperwork and an impromptu meeting with a colleague and her client. Of all the times he could’ve been late for anything, he was so pissed it was for this. As he took the exit for the airport, he forced his shoulders to relax and his breath to come in deep and even. Who’s to say whatever was waiting for him at that stupid steakhouse wouldn’t make him grateful he was late to begin with? Maybe seeing Jake again and being dished up some catastrophe (and he was sure it could be nothing short of a major disaster) would make him want to spin on his heels and run right out the door.

As he pulled into the busy expanse of airport parking lot and finally weaved his way through the traveling masses and into the monstrously ugly building, the thought of abandoning ship left his thoughts completely. The only thing he could picture now was Jake’s face, but when he nearly careened into the steakhouse entrance, almost knocking the hostess off her feet, the Jake his eyes almost immediately latched onto was not the man he had previous known; or, at least, he didn’t look like him.

The man sitting hunched and tense at the bar had his hair buzzed short and dyed a dark brown; he was casually dressed, and Dean recognized the black jacket he was wearing (one of Jake’s favorites), but the way his clothes sat on him, slightly looser than years before, made that sense of dread Dean had been trying to keep on the backburner slither to the forefront of his brain. He could only see Jake’s profile, and the only bit of solace Dean could glean was in the unmistakable contour of the man’s jaw line, the gentle slope of his cheekbones, and the arch of his nose; it was still, without a doubt, Jake Royer.

Dean ignored the hostess’ confused inquisitions and made his way through the maze of diners, only to come to a halt behind the stool right next to Jake’s side. Jake had been in the process of raising a glass of what must have been whiskey to his lips when his eyes caught the stranger standing next to him. The glass stopped halfway to its destination and Jake’s expression slowly morphed into recognition and then something else, something warm and altogether sincere. He set his glass down and rose from his stool, but the both of them stood awkwardly for several seconds, perhaps not knowing or trusting themselves to break the silence with words. Finally Jake’s lips turned up into a small grin, genuine but mostly cheerless. They sank back into the bar chairs and Jake motioned to the bartender who promptly fixed a drink and slid it over to Dean, who stared at the amber liquid rippling in the glass with something like nostalgia. He couldn’t help but chuckle as he picked it up and took a swig,

“JD.” He said, matter-of-factly, “My vice. Thanks, man.” Jake nodded, his smile widening,

“Least I can do.” Jake murmured, his voice as deep as before, but gravelly, a note more severe than Dean had ever heard it before, 

“Thanks for coming out here, Dean.” Jake started, and it seemed as if he were going to say more, but he didn’t, leaving Dean in a lurch he wasn’t expecting.

“Don’t mention it.” He put the glass down, becoming serious, “Whatever I can do, man, name it.” At this, Jake leaned back on his stool, his eyes skittering away and his jaw tight; it was weird seeing him with a buzz-cut and a dye job that he never once thought Jake would ever consider. But, again, Dean thought, that was probably the point; the other man hadn’t changed his look for kicks, he was sure. All things considered, Jake still possessed that aesthetic charm that was all his own; his eyes were still a thrilling brown and his smiles still as infectious as ever. From what Dean could make out, it also looked like there was still hard, sinewy muscle under his jacket and gray flannel shirt. It was evident, though, that whatever trouble Jake had found himself in was eating him from the inside out. After a long pause, Dean watched as Jake’s eyebrows came together in the pained expression he adopted when he wasn’t sure about something,

“…Dean,” he finally said, his exasperation hardly masked, “I don’t know if I can ask you to do this though—“ He ran a hand over his short hair but found no purchase; this was something he did when it had been longer, when he had been able to tangle his fingers into it. Dean had always called it his tell and ribbed him mercilessly about it whenever they played poker. A part of Dean recoiled inside as these little memories came back to him; the fact that he could still recall those habits and mannerisms that once seemed so mundane and insignificant stung worse than he could think possible. He let out a harsh laugh and could almost see his frown reflected in Jake’s open stare.

“You can’t fucking do that,” He gritted out, “not now that I know something’s going on… I know you’ve pulled some shit, _David Larson_ , so you can’t tell me to just let this go.” At the alias, Jake’s gaze snapped up to meet his in surprise, but the shock was short-lived; resignation took its place and then his expression went blank. Dean’s tone left no possible way out for either of them, so Jake leaned forward on his elbows and took a moment to collect his thoughts, his penetrative gaze studying Dean with something unreadable,

“…Started two months ago.” He began reluctantly, his voice low, “I was working a job over in Aurora, under the name David Larson, when…” He ran his fingers over the counter in jerky motions, his eyes falling from Dean’s stare, “…Benny sent me a copy of some documents.” At the mention of Benny’s name, Dean immediately went tense, his face turning into a dark scowl. Benny Lafitte had been one of Dean’s closest friends, one of the first colleagues he had made when he started out in the business years ago; now the thought of Benny only made Dean angry. He couldn’t help but ask the only question that came into his mind; his tone was low and gruff, almost warningly so,

“You guys still…?” He couldn’t bring himself to say more. Jake’s look was inscrutable, if not somewhat irritated,

“No.” He replied shortly. Dean couldn’t help the malicious tinge of satisfaction that ran up his spine at the news; he kept his expression painfully neutral though, and simply let out a contemplative and curt ‘hmm’. Dean could sense the aggravated buzz emanating from Jake like a heat wave, but Jake went on as if Dean’s little interjection had never taken place,

“The document is some kind of contract…or a series of contracts…between SucroCorp and some other corporations—all big players, no bullshit—but the point is, there is no way Roman would want these documents getting in the wrong hands. They could destroy him.” Jake downed the rest of his whiskey in one go and hissed, 

“I don’t know who Benny was working for, or why he got them, or how, but I haven’t heard anything from him since he sent them my way…” Jake licked his lips and scrubbed his hand over his face, and, for the first time, Dean caught a glimpse of the dark circles under Jake’s eyes, the way his skin was much paler than the deceptively warm hues cast over him by the bar lights, the way he seemed gaunt where the shadows sat deep and angular on his features…

“Well, what the fuck, Jake…” He nodded his head meaninglessly, trying to will words to come out of his mouth, words that would make all of this disappear, 

“…Roman can’t know who you are. I know you’re too careful for that…” Dean offered as consolation; he licked his lips, shifted in his chair, fear coiling in his gut, “…lose the papers. Cover your tracks. Get out of Chicago—”

“It’s too late, Dean.” Jake was shaking his head vigorously; his eyes reflecting the fear crawling under Dean’s skin in double measure: there was something like despair there, and a desperation blazing like fire, “They know it’s me. I tried to play it off—gave them some false information to try and get them off my trail, and I thought it worked...” Suddenly he wouldn’t look at Dean and his fists were clenched white in his lap, “But they fucking _killed_ my brother and his wife—”

“ _What?!_ ” Dean jerked forward in his chair feeling as if the muscles in his body had been injected with a current of electricity. Jake didn’t even bother to look around to see if people had taken notice of the outburst, but his voice, now trembling, was lower,

“They never even warned me! Roman means business and he made it way too fucking clear there won’t be any bullshitting around…” He hesitated a moment, catching his lower lip in an anxious bite, “My family thinks I’m a fuckin' _travel agent_ , Dean!” He groaned, “They had no clue! And those bastards just—” his voice hitched and he wasn’t able to continue. Dean had only ever seen Jake cry once, and that was when his father died four years ago, but the hunch in Jake’s shoulders and the way his jaw was set so tight was evidence enough that it was taking all he had not to let the tears come, and Dean couldn’t help but reach out instinctively. His hand came to grasp the sleeve of Jake’s jacket, half marveling at the fact that he couldn’t bring himself to take Jake’s hand, to feel his skin, no matter how much he wanted to. Jake took in a deep, shuddering breath and ran his hand slowly over his eyes once,

“Point is,” He started again, his voice measured and painfully neutral, “I’m finishing this. I made copies of the papers…I put one in a safe deposit box and sent the key to Garth. I didn’t tell him anything, just that…if anything should happen to me, to open it.” He sighed heavily, “I also sent a copy to a proprietor overseas, Bela Talbot. She’s got some beef with Roman that works fine for me. She said she’d leak it to the press if I don’t turn up.” Jake paused to order another round of whiskey as the bartender came by, “I told Roman if he so much as looks my way I’ll have someone drop the bomb on his little fucking empire.” He growls, “All I need now is to get out of here. I need to lay low and plan the next move. I don’t think Roman will try anything else, at least not right away, but fuck if I let him get a step ahead of me again.” He’s bitter and his expression is twisted in a way Dean’s never seen it before; it hurts him to watch this transformation in Jake, or, rather, to have been left in its wake. All he can manage to say is,

“Why’d you wait this long to tell me?” It comes out as a whisper, more than anything else, and the tone implies much more left unsaid. Jake watches him carefully for a long moment, his demeanor unsympathetic but strangely soft, as if he can’t quite decide which he’d prefer to be,

“I ditched my place, got rid of my cell-phone, and I’ve been using only cash and rotating between a few names…But I need your help to get out of Chicago; I can’t get a hold of Frank, the son-of-a-bitch.” He ignores Dean’s question entirely, and Dean lets it go. The insult about Frank is said without much heat, as if Jake knows getting a hold of Frank at a time like this is highly improbable to begin with. “I wanted him to make me a couple new fake IDs, but he’s probably skipped town without me,” he chuckled humorlessly, “just need a few connections, you know, to help me stay off the radar for a bit.”  
Dean is silent for a long time, his knuckles wrapping lightly against the counter top.

“Yeah, ok.” And Jake has the audacity to look genuinely surprised, and this makes Dean angrier than he thought possible, “What?” He snaps,

“I just didn’t think you’d…”

“Did you think I’d just throw you under the bus, Jake?” Dean lets the anger melt away, but the keen sense of betrayal he still feels like the prick of a needle, “Christ! You think I’d just sit back and do nothing—”

“ _No_. I just didn’t think you’d be that easy to convince—” and before Dean can cut him off with a bitter interjection, Jake goes on, his cadence hurried and anxious “—because this is my mess, ok?”

“Actually, no, it wasn’t your mess until Benny dropped it on you.”

“Damn it, Dean!” And Jake struggles to keep his voice down, “That’s not the _point_!” He takes a deep breath and the look he gives Dean stops him dead in his tracks. Jake’s expression is filled with regret and empathy and, if Dean didn’t know any better, affection. It’s genuine, unrefined, and harbors a hint of the intimate sincerity he had once been so used to,

“Trust me, Dean,” Jake whispers, his voice wavering slightly, “If I could keep you out of this shit, I would.” He swallows back whatever else he might say and his hand brushes quickly over Dean’s fingertips, “I just didn’t know who else I could really trust.” As Jake finishes, the words tumbling out of him like a confession, Dean sucks in a deep breath he hopes is soundless. He feels like an idiot; a part of him had wanted so badly to blame Jake for all this, but he can’t, not now, not ever.

“Well you can trust me.” Dean says, and it’s the most decisive thing he’s said all night. They study each other for a long moment, gauging each other, weighing the newest development in their unexpected situation.

“I’ve got a place you can skip town to. It’s far enough out in the middle of nowhere Roman would have to sell his soul to find your ass, and, if push comes to shove, the Canadian border’s only a couple hours away.” Dean finally says, and there’s something off about his tone, but Jake doesn’t push it. He’s good about that sort of thing, although Dean realizes the coin always has two sides. Jake looks relieved, and again runs his hand over his short spikes. Dean gives him a tentative smile, slaps him on the arm,

“It’ll be ok.” He says, and his voice sounds a lot more reassuring than he actually thinks it should. “Come on. Let’s get out of here.”

**Author's Note:**

> I don't know if I'm way over my head here or what, but I wanted to give this a shot. Those with OTP OCD will definitely have a hard time with this story, but please give it a chance! :)
> 
> It's way unconventional and so far off the deep end (Canon? What's that?), I know. 
> 
> Tell me what you think though! Your feedback is much appreciated!


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